# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Toshio Kawato' 'Kilchi Aminmotot' 'Hisatane Fukuda' 'Hiroyuki Koyama' _publ_contact_author_name 'Prof Toshio Kawato' _publ_contact_author_address ; Department of Chemistry Faculty of Sciences, Kyushu University 4-2-1 Ropponmatsu, Chuo-ku Fukuoka 810-8560 JAPAN ; _publ_contact_author_email KAWATO@CHEM.RC.KYUSHU-U.AC.JP _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Crystalline photochromism of N-salicylidene-2,6-dialkylanilines: advantage of 2,6-dialkyl substituents of aniline for preparation of photochromic Schiff base crystals ; data_1a _database_code_CSD 200498 _audit_creation_date 2002-12-07T08:03:40-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; N-3,5-dichlorosalicylideneaniline ; _chemical_formula_moiety 'C13 H9 Cl2 N1 O1' _chemical_formula_sum 'C13 H9 Cl2 N O' _chemical_formula_weight 266.11 _chemical_compound_source 'synthesis as described' _chemical_melting_point 379 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.5249(2) _cell_length_b 19.1440(9) _cell_length_c 13.5302(4) _cell_angle_alpha 90 _cell_angle_beta 94.7150(10) _cell_angle_gamma 90 _cell_volume 1168.08(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.535 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_unetI/netI 0.0242 _diffrn_reflns_number 9823 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.98 _diffrn_measured_fraction_theta_max 0.98 _reflns_number_total 2616 _reflns_number_gt 2297 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Rigaku RAXIS-IV' _computing_cell_refinement 'Rigaku RAXIS-IV' _computing_data_reduction 'Rigaku RAXIS-IV' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0815P)^2^+18.9372P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.012(4) _refine_ls_number_reflns 2616 _refine_ls_number_parameters 179 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1217 _refine_ls_R_factor_gt 0.1115 _refine_ls_wR_factor_ref 0.3322 _refine_ls_wR_factor_gt 0.3221 _refine_ls_goodness_of_fit_ref 1.17 _refine_ls_restrained_S_all 1.169 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.83 _refine_diff_density_min -0.694 _refine_diff_density_rms 0.184 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.2821(17) 0.2392(4) 0.1845(6) 0.0276(16) Uani 1 1 d D . . C2 C -0.1611(16) 0.2259(4) 0.2809(5) 0.0254(15) Uani 1 1 d D . . C3 C 0.0521(16) 0.1719(4) 0.2960(6) 0.0261(15) Uani 1 1 d D . . C4 C 0.1419(17) 0.1340(4) 0.2170(6) 0.0287(16) Uani 1 1 d D . . C5 C 0.0221(17) 0.1478(4) 0.1211(6) 0.0292(16) Uani 1 1 d D . . C6 C -0.1901(18) 0.1999(4) 0.1051(6) 0.0295(17) Uani 1 1 d D . . C7 C -0.5066(18) 0.2931(4) 0.1649(6) 0.0287(16) Uani 1 1 d . . . C8 C -0.8099(16) 0.3836(4) 0.2164(6) 0.0257(15) Uani 1 1 d D . . C9 C -0.9142(17) 0.4143(4) 0.3004(6) 0.0289(16) Uani 1 1 d D . . C10 C -1.125(2) 0.4681(4) 0.2891(7) 0.0353(18) Uani 1 1 d D . . C11 C -1.2320(19) 0.4905(4) 0.1963(7) 0.0340(18) Uani 1 1 d D . . C12 C -1.1215(19) 0.4602(4) 0.1124(7) 0.0338(18) Uani 1 1 d D . . C13 C -0.9146(18) 0.4079(4) 0.1223(6) 0.0317(17) Uani 1 1 d D . . Cl1 Cl 0.1935(5) 0.15241(11) 0.41464(15) 0.0375(6) Uani 1 1 d . . . Cl2 Cl 0.1375(6) 0.09940(12) 0.02395(16) 0.0428(7) Uani 1 1 d . . . O1 O -0.2340(14) 0.2623(3) 0.3597(4) 0.0351(14) Uani 1 1 d . . . N1 N -0.5939(14) 0.3301(3) 0.2345(5) 0.0279(14) Uani 1 1 d . . . H1 H -0.39(3) 0.297(8) 0.330(11) 0.10(5) Uiso 1 1 d . . . H2 H 0.303(18) 0.098(4) 0.227(6) 0.02(2) Uiso 1 1 d . . . H3 H -0.2724 0.209 0.0393 0.036 Uiso 1 1 d . . . H4 H -0.5886 0.3008 0.0989 0.035 Uiso 1 1 d . . . H5 H -0.830(17) 0.400(4) 0.369(6) 0.019(19) Uiso 1 1 d . . . H6 H -1.16(2) 0.485(6) 0.354(8) 0.06(3) Uiso 1 1 d . . . H7 H -1.37(2) 0.524(5) 0.188(7) 0.03(2) Uiso 1 1 d . . . H8 H -1.20(2) 0.481(5) 0.050(7) 0.04(3) Uiso 1 1 d . . . H9 H -0.8415 0.388 0.0646 0.038 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.027(4) 0.024(3) 0.031(4) 0.000(3) -0.001(3) 0.000(3) C2 0.028(4) 0.024(3) 0.026(4) 0.001(3) 0.008(3) -0.004(3) C3 0.025(4) 0.025(4) 0.028(4) 0.004(3) 0.000(3) -0.002(3) C4 0.028(4) 0.022(3) 0.035(4) 0.005(3) -0.003(3) -0.003(3) C5 0.030(4) 0.029(4) 0.030(4) -0.002(3) 0.007(3) 0.000(3) C6 0.031(4) 0.030(4) 0.026(4) 0.005(3) 0.000(3) -0.004(3) C7 0.029(4) 0.027(4) 0.030(4) 0.004(3) 0.002(3) -0.003(3) C8 0.021(3) 0.023(3) 0.033(4) 0.001(3) 0.001(3) -0.004(3) C9 0.029(4) 0.028(4) 0.030(4) -0.002(3) 0.008(3) -0.006(3) C10 0.039(5) 0.031(4) 0.037(4) -0.003(3) 0.007(4) -0.004(3) C11 0.030(4) 0.025(4) 0.047(5) 0.002(3) 0.003(4) 0.000(3) C12 0.032(4) 0.031(4) 0.039(5) 0.003(3) 0.002(4) -0.001(3) C13 0.030(4) 0.032(4) 0.033(4) -0.001(3) 0.001(3) 0.002(3) Cl1 0.0458(12) 0.0368(11) 0.0286(10) 0.0033(8) -0.0046(8) 0.0055(9) Cl2 0.0532(14) 0.0423(12) 0.0329(11) -0.0080(9) 0.0040(9) 0.0123(10) O1 0.045(3) 0.035(3) 0.025(3) -0.002(2) 0.001(3) 0.005(3) N1 0.025(3) 0.027(3) 0.031(3) -0.002(3) 0.001(3) -0.001(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.395(11) . ? C1 C6 1.404(11) . ? C1 C7 1.457(11) . ? C2 O1 1.337(9) . ? C2 C3 1.418(10) . ? C3 C4 1.379(11) . ? C3 Cl1 1.720(8) . ? C4 C5 1.390(11) . ? C4 H2 1.00(8) . ? C5 C6 1.389(11) . ? C5 Cl2 1.724(8) . ? C6 H3 0.952(8) . ? C7 N1 1.268(10) . ? C7 H4 0.950(8) . ? C8 C9 1.396(11) . ? C8 C13 1.402(11) . ? C8 N1 1.424(9) . ? C9 C10 1.403(12) . ? C9 H5 1.02(8) . ? C10 C11 1.377(13) . ? C10 H6 0.95(11) . ? C11 C12 1.403(12) . ? C11 H7 0.89(9) . ? C12 C13 1.369(11) . ? C12 H8 0.97(10) . ? C13 H9 0.952(8) . ? O1 H1 1.03(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.0(7) . . ? C2 C1 C7 120.9(7) . . ? C6 C1 C7 119.1(7) . . ? O1 C2 C1 123.1(7) . . ? O1 C2 C3 118.3(7) . . ? C1 C2 C3 118.5(7) . . ? C4 C3 C2 120.8(7) . . ? C4 C3 Cl1 119.9(6) . . ? C2 C3 Cl1 119.3(6) . . ? C3 C4 C5 120.4(7) . . ? C3 C4 H2 121(5) . . ? C5 C4 H2 119(5) . . ? C6 C5 C4 119.6(7) . . ? C6 C5 Cl2 121.0(6) . . ? C4 C5 Cl2 119.4(6) . . ? C5 C6 C1 120.7(7) . . ? C5 C6 H3 119.4(8) . . ? C1 C6 H3 119.9(8) . . ? N1 C7 C1 121.0(7) . . ? N1 C7 H4 119.4(8) . . ? C1 C7 H4 119.6(8) . . ? C9 C8 C13 119.2(7) . . ? C9 C8 N1 115.9(7) . . ? C13 C8 N1 124.9(7) . . ? C8 C9 C10 119.6(8) . . ? C8 C9 H5 120(5) . . ? C10 C9 H5 120(4) . . ? C11 C10 C9 120.8(8) . . ? C11 C10 H6 131(7) . . ? C9 C10 H6 108(7) . . ? C10 C11 C12 119.2(8) . . ? C10 C11 H7 121(6) . . ? C12 C11 H7 119(6) . . ? C13 C12 C11 120.6(8) . . ? C13 C12 H8 125(6) . . ? C11 C12 H8 115(6) . . ? C12 C13 C8 120.6(8) . . ? C12 C13 H9 119.6(8) . . ? C8 C13 H9 119.8(8) . . ? C2 O1 H1 104(8) . . ? C7 N1 C8 121.7(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 O1 178.6(7) . . . . ? C7 C1 C2 O1 -2.2(10) . . . . ? C6 C1 C2 C3 -0.6(9) . . . . ? C7 C1 C2 C3 178.7(7) . . . . ? O1 C2 C3 C4 -178.2(7) . . . . ? C1 C2 C3 C4 1.0(9) . . . . ? O1 C2 C3 Cl1 3.2(8) . . . . ? C1 C2 C3 Cl1 -177.6(5) . . . . ? C2 C3 C4 C5 -0.6(11) . . . . ? Cl1 C3 C4 C5 177.9(6) . . . . ? C3 C4 C5 C6 -0.3(12) . . . . ? C3 C4 C5 Cl2 -179.8(6) . . . . ? C4 C5 C6 C1 0.8(12) . . . . ? Cl2 C5 C6 C1 -179.8(6) . . . . ? C2 C1 C6 C5 -0.3(11) . . . . ? C7 C1 C6 C5 -179.6(7) . . . . ? C2 C1 C7 N1 1.3(11) . . . . ? C6 C1 C7 N1 -179.5(7) . . . . ? C13 C8 C9 C10 1.1(9) . . . . ? N1 C8 C9 C10 179.3(7) . . . . ? C8 C9 C10 C11 0.5(10) . . . . ? C9 C10 C11 C12 -1.7(12) . . . . ? C10 C11 C12 C13 1.4(12) . . . . ? C11 C12 C13 C8 0.2(12) . . . . ? C9 C8 C13 C12 -1.5(11) . . . . ? N1 C8 C13 C12 -179.5(7) . . . . ? C1 C7 N1 C8 179.1(7) . . . . ? C9 C8 N1 C7 172.1(7) . . . . ? C13 C8 N1 C7 -9.8(11) . . . . ? #===END data_1b _database_code_CSD 200499 _audit_creation_date 2002-12-07T07:37:38-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; N-(3,5-dichlorosalicylidene)-2,6-dimethylaniline ; _chemical_formula_moiety 'C15 H13 Cl2 N1 O1' _chemical_formula_sum 'C15 H13 Cl2 N O' _chemical_formula_weight 294.16 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.7170(10) _cell_length_b 9.179(3) _cell_length_c 13.527(2) _cell_angle_alpha 90 _cell_angle_beta 116.965(9) _cell_angle_gamma 90 _cell_volume 1407.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.452 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_unetI/netI 0.018 _diffrn_reflns_number 3370 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 3233 _reflns_number_gt 2569 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Rigaku AFC-7R' _computing_cell_refinement 'Rigaku AFC-7R' _computing_data_reduction 'Rigaku AFC-7R' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.3518P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0023(13) _refine_ls_number_reflns 3233 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.1056 _refine_ls_wR_factor_gt 0.0965 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.203 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.038 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.00263(14) 0.01747(18) 0.22095(13) 0.0423(3) Uani 1 1 d . . . C2 C -0.00899(14) 0.10171(17) 0.12964(13) 0.0403(3) Uani 1 1 d . . . C3 C 0.09326(14) 0.13772(17) 0.12119(13) 0.0422(3) Uani 1 1 d . . . C4 C 0.20354(15) 0.0934(2) 0.19898(14) 0.0480(4) Uani 1 1 d . . . C5 C 0.21219(14) 0.0088(2) 0.28722(14) 0.0490(4) Uani 1 1 d . . . C6 C 0.11397(15) -0.0286(2) 0.29947(15) 0.0491(4) Uani 1 1 d . . . C7 C -0.10144(15) -0.02493(19) 0.23328(15) 0.0468(4) Uani 1 1 d . . . C8 C -0.30294(13) -0.03540(18) 0.18063(13) 0.0422(3) Uani 1 1 d . . . C9 C -0.31577(15) 0.01206(19) 0.27321(13) 0.0458(4) Uani 1 1 d . . . C10 C -0.2311(2) 0.1176(3) 0.35694(19) 0.0616(5) Uani 1 1 d . . . C11 C -0.41218(17) -0.0381(2) 0.28519(16) 0.0546(4) Uani 1 1 d . . . C12 C -0.49328(18) -0.1310(2) 0.20880(18) 0.0625(5) Uani 1 1 d . . . C13 C -0.48107(18) -0.1729(2) 0.11682(18) 0.0618(5) Uani 1 1 d . . . C14 C -0.38666(15) -0.1254(2) 0.10012(14) 0.0495(4) Uani 1 1 d . . . C15 C -0.3737(2) -0.1729(3) -0.0002(2) 0.0690(6) Uani 1 1 d . . . Cl1 Cl 0.08016(4) 0.24376(5) 0.00988(4) 0.05750(16) Uani 1 1 d . . . Cl2 Cl 0.35038(4) -0.05208(7) 0.38436(4) 0.0733(2) Uani 1 1 d . . . N1 N -0.20532(12) 0.01159(16) 0.16320(12) 0.0457(3) Uani 1 1 d . . . O1 O -0.11428(10) 0.14741(14) 0.05198(10) 0.0516(3) Uani 1 1 d . . . H1 H -0.167(2) 0.109(3) 0.073(2) 0.087(8) Uiso 1 1 d . . . H4 H 0.2711(18) 0.118(2) 0.1898(16) 0.057(5) Uiso 1 1 d . . . H6 H 0.1212(19) -0.088(2) 0.3627(18) 0.065(6) Uiso 1 1 d . . . H7 H -0.0857(18) -0.085(2) 0.2965(17) 0.057(5) Uiso 1 1 d . . . H10A H -0.160(3) 0.069(3) 0.410(2) 0.093(8) Uiso 1 1 d . . . H10B H -0.206(2) 0.197(3) 0.321(2) 0.088(8) Uiso 1 1 d . . . H10C H -0.262(3) 0.160(3) 0.403(3) 0.112(10) Uiso 1 1 d . . . H11 H -0.4220(18) -0.006(2) 0.3513(17) 0.061(6) Uiso 1 1 d . . . H12 H -0.560(2) -0.163(3) 0.218(2) 0.083(7) Uiso 1 1 d . . . H13 H -0.539(2) -0.234(3) 0.062(2) 0.076(7) Uiso 1 1 d . . . H15A H -0.314(3) -0.244(3) 0.018(2) 0.094(9) Uiso 1 1 d . . . H15B H -0.350(3) -0.088(4) -0.030(2) 0.108(10) Uiso 1 1 d . . . H15C H -0.444(3) -0.204(4) -0.056(3) 0.112(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0405(8) 0.0417(8) 0.0458(8) 0.0033(6) 0.0205(7) 0.0009(6) C2 0.0409(8) 0.0377(8) 0.0421(8) 0.0006(6) 0.0186(6) 0.0008(6) C3 0.0472(8) 0.0406(8) 0.0435(8) 0.0002(6) 0.0247(7) -0.0008(7) C4 0.0414(8) 0.0556(10) 0.0516(9) -0.0005(7) 0.0253(7) 0.0000(7) C5 0.0380(8) 0.0590(10) 0.0477(9) 0.0061(7) 0.0175(7) 0.0091(7) C6 0.0462(9) 0.0537(10) 0.0480(9) 0.0110(8) 0.0218(7) 0.0060(7) C7 0.0444(9) 0.0471(9) 0.0518(9) 0.0084(7) 0.0243(7) -0.0005(7) C8 0.0379(7) 0.0453(8) 0.0450(8) 0.0014(7) 0.0201(6) -0.0026(6) C9 0.0447(8) 0.0482(9) 0.0426(8) -0.0032(7) 0.0182(7) -0.0027(7) C10 0.0548(11) 0.0681(13) 0.0557(11) -0.0176(10) 0.0198(9) -0.0096(10) C11 0.0572(10) 0.0636(11) 0.0512(9) -0.0065(8) 0.0319(8) -0.0060(9) C12 0.0553(11) 0.0743(13) 0.0716(12) -0.0115(10) 0.0407(10) -0.0180(10) C13 0.0525(10) 0.0715(13) 0.0653(12) -0.0227(10) 0.0302(9) -0.0226(9) C14 0.0465(9) 0.0566(10) 0.0483(9) -0.0088(8) 0.0239(7) -0.0066(8) C15 0.0681(14) 0.0886(17) 0.0585(12) -0.0244(12) 0.0359(11) -0.0149(13) Cl1 0.0613(3) 0.0642(3) 0.0549(3) 0.0129(2) 0.0333(2) 0.0001(2) Cl2 0.0426(2) 0.1057(5) 0.0671(3) 0.0235(3) 0.0209(2) 0.0209(3) N1 0.0401(7) 0.0499(8) 0.0488(7) 0.0020(6) 0.0218(6) -0.0037(6) O1 0.0414(6) 0.0596(7) 0.0501(7) 0.0146(6) 0.0175(5) 0.0043(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.396(2) . ? C1 C2 1.407(2) . ? C1 C7 1.460(2) . ? C2 O1 1.3404(19) . ? C2 C3 1.396(2) . ? C3 C4 1.379(2) . ? C3 Cl1 1.7362(16) . ? C4 C5 1.386(3) . ? C4 H4 0.95(2) . ? C5 C6 1.376(2) . ? C5 Cl2 1.7414(17) . ? C6 H6 0.98(2) . ? C7 N1 1.273(2) . ? C7 H7 0.96(2) . ? C8 C14 1.396(2) . ? C8 C9 1.404(2) . ? C8 N1 1.4312(19) . ? C9 C11 1.386(2) . ? C9 C10 1.508(3) . ? C10 H10A 0.98(3) . ? C10 H10B 1.00(3) . ? C10 H10C 0.96(3) . ? C11 C12 1.376(3) . ? C11 H11 1.00(2) . ? C12 C13 1.377(3) . ? C12 H12 0.96(3) . ? C13 C14 1.389(3) . ? C13 H13 0.96(2) . ? C14 C15 1.504(3) . ? C15 H15A 0.95(3) . ? C15 H15B 0.99(3) . ? C15 H15C 0.91(3) . ? O1 H1 0.91(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 120.06(15) . . ? C6 C1 C7 119.46(15) . . ? C2 C1 C7 120.47(14) . . ? O1 C2 C3 119.89(14) . . ? O1 C2 C1 122.00(14) . . ? C3 C2 C1 118.11(14) . . ? C4 C3 C2 122.05(15) . . ? C4 C3 Cl1 119.44(13) . . ? C2 C3 Cl1 118.50(12) . . ? C3 C4 C5 118.59(15) . . ? C3 C4 H4 119.9(12) . . ? C5 C4 H4 121.5(12) . . ? C6 C5 C4 121.43(15) . . ? C6 C5 Cl2 119.33(14) . . ? C4 C5 Cl2 119.23(13) . . ? C5 C6 C1 119.74(16) . . ? C5 C6 H6 120.8(13) . . ? C1 C6 H6 119.5(13) . . ? N1 C7 C1 122.23(16) . . ? N1 C7 H7 122.8(12) . . ? C1 C7 H7 115.0(12) . . ? C14 C8 C9 121.57(14) . . ? C14 C8 N1 117.47(14) . . ? C9 C8 N1 120.92(14) . . ? C11 C9 C8 117.90(15) . . ? C11 C9 C10 119.57(17) . . ? C8 C9 C10 122.51(16) . . ? C9 C10 H10A 111.6(16) . . ? C9 C10 H10B 112.1(15) . . ? H10A C10 H10B 107(2) . . ? C9 C10 H10C 112.5(19) . . ? H10A C10 H10C 103(2) . . ? H10B C10 H10C 110(2) . . ? C12 C11 C9 121.31(17) . . ? C12 C11 H11 119.9(12) . . ? C9 C11 H11 118.8(12) . . ? C11 C12 C13 119.91(17) . . ? C11 C12 H12 119.8(15) . . ? C13 C12 H12 120.2(15) . . ? C12 C13 C14 121.29(18) . . ? C12 C13 H13 120.2(15) . . ? C14 C13 H13 118.5(15) . . ? C13 C14 C8 117.94(16) . . ? C13 C14 C15 120.80(17) . . ? C8 C14 C15 121.24(17) . . ? C14 C15 H15A 111.4(18) . . ? C14 C15 H15B 108.5(17) . . ? H15A C15 H15B 108(2) . . ? C14 C15 H15C 112(2) . . ? H15A C15 H15C 112(3) . . ? H15B C15 H15C 105(3) . . ? C7 N1 C8 118.87(15) . . ? C2 O1 H1 104.2(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 O1 179.56(16) . . . . ? C7 C1 C2 O1 0.8(2) . . . . ? C6 C1 C2 C3 -0.5(2) . . . . ? C7 C1 C2 C3 -179.23(15) . . . . ? O1 C2 C3 C4 179.93(15) . . . . ? C1 C2 C3 C4 0.0(2) . . . . ? O1 C2 C3 Cl1 0.8(2) . . . . ? C1 C2 C3 Cl1 -179.12(12) . . . . ? C2 C3 C4 C5 1.0(3) . . . . ? Cl1 C3 C4 C5 -179.96(14) . . . . ? C3 C4 C5 C6 -1.4(3) . . . . ? C3 C4 C5 Cl2 178.37(13) . . . . ? C4 C5 C6 C1 0.9(3) . . . . ? Cl2 C5 C6 C1 -178.86(14) . . . . ? C2 C1 C6 C5 0.0(3) . . . . ? C7 C1 C6 C5 178.81(17) . . . . ? C6 C1 C7 N1 -178.67(17) . . . . ? C2 C1 C7 N1 0.1(3) . . . . ? C14 C8 C9 C11 2.7(3) . . . . ? N1 C8 C9 C11 -179.78(16) . . . . ? C14 C8 C9 C10 -175.58(18) . . . . ? N1 C8 C9 C10 2.0(3) . . . . ? C8 C9 C11 C12 -0.3(3) . . . . ? C10 C9 C11 C12 178.0(2) . . . . ? C9 C11 C12 C13 -1.7(3) . . . . ? C11 C12 C13 C14 1.2(4) . . . . ? C12 C13 C14 C8 1.1(3) . . . . ? C12 C13 C14 C15 179.5(2) . . . . ? C9 C8 C14 C13 -3.1(3) . . . . ? N1 C8 C14 C13 179.30(18) . . . . ? C9 C8 C14 C15 178.6(2) . . . . ? N1 C8 C14 C15 0.9(3) . . . . ? C1 C7 N1 C8 179.44(15) . . . . ? C14 C8 N1 C7 -118.36(19) . . . . ? C9 C8 N1 C7 64.0(2) . . . . ? #===END data_1d _database_code_CSD 200500 _audit_creation_date 2002-12-07T08:06:58-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; N-(3,5-dichlorosalicylidene)-2,6-diisopropylaniline ; _chemical_formula_moiety 'C19 H21 Cl2 N1 O1' _chemical_formula_sum 'C19 H21 Cl2 N O' _chemical_formula_weight 350.27 _chemical_compound_source 'synthesis as described' _chemical_melting_point 391 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.2280(7) _cell_length_b 14.8658(8) _cell_length_c 22.7359(13) _cell_angle_alpha 90 _cell_angle_beta 91.153(3) _cell_angle_gamma 90 _cell_volume 3794.2(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.346 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_unetI/netI 0.0229 _diffrn_reflns_number 33356 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _reflns_number_total 8606 _reflns_number_gt 5585 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Rigaku RAXIS-IV' _computing_cell_refinement 'Rigaku RAXIS-IV' _computing_data_reduction 'Rigaku RAXIS-IV' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0834P)^2^+1.2854P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0000(3) _refine_ls_number_reflns 8606 _refine_ls_number_parameters 488 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0997 _refine_ls_R_factor_gt 0.0614 _refine_ls_wR_factor_ref 0.19 _refine_ls_wR_factor_gt 0.1601 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_restrained_S_all 1.06 _refine_ls_shift/su_max 0.879 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 0.289 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.052 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.38817(10) -0.27577(6) 0.02402(4) 0.1034(3) Uani 1 1 d . . . Cl2 Cl -0.07109(9) -0.25525(7) 0.08498(4) 0.1035(3) Uani 1 1 d . . . Cl3 Cl 0.84898(8) 0.52881(6) 0.01487(5) 0.1011(3) Uani 1 1 d . . . Cl4 Cl 0.40535(7) 0.50183(6) 0.09790(4) 0.0893(3) Uani 1 1 d . . . O1 O 0.41316(18) -0.11047(15) 0.09038(9) 0.0751(5) Uani 1 1 d . . . H1 H 0.412(3) -0.061(2) 0.1103(14) 0.087(10) Uiso 1 1 d . . . O2 O 0.89101(17) 0.36465(15) 0.08064(9) 0.0732(5) Uani 1 1 d . . . H2 H 0.892(3) 0.314(2) 0.0990(14) 0.084(10) Uiso 1 1 d . . . N1 N 0.33298(18) 0.02343(13) 0.15175(9) 0.0583(5) Uani 1 1 d . . . N2 N 0.82560(19) 0.22873(14) 0.14573(9) 0.0612(5) Uani 1 1 d . . . C1 C 0.2098(2) -0.09812(16) 0.11923(10) 0.0563(6) Uani 1 1 d . . . C2 C 0.3018(2) -0.14222(16) 0.09057(10) 0.0588(6) Uani 1 1 d . . . C3 C 0.2756(3) -0.22215(18) 0.06055(11) 0.0706(7) Uani 1 1 d . . . C4 C 0.1615(3) -0.2565(2) 0.05872(12) 0.0757(9) Uani 1 1 d . . . H4 H 0.147(3) -0.311(2) 0.0362(14) 0.098(10) Uiso 1 1 d . . . C5 C 0.0724(3) -0.2116(2) 0.08699(11) 0.0703(8) Uani 1 1 d . . . C6 C 0.0949(3) -0.13360(19) 0.11671(11) 0.0650(7) Uani 1 1 d . . . H6 H 0.035(2) -0.1039(17) 0.1367(11) 0.061(8) Uiso 1 1 d . . . C7 C 0.2306(2) -0.01315(17) 0.14980(11) 0.0580(6) Uani 1 1 d . . . H7 H 0.162(2) 0.0143(17) 0.1697(11) 0.062(7) Uiso 1 1 d . . . C8 C 0.3466(2) 0.10952(16) 0.17941(10) 0.0553(6) Uani 1 1 d . . . C9 C 0.4079(2) 0.11329(18) 0.23342(11) 0.0667(7) Uani 1 1 d . . . C10 C 0.4541(3) 0.0286(2) 0.26344(16) 0.0892(10) Uani 1 1 d . . . H10 H 0.483(4) -0.013(3) 0.2307(19) 0.140(16) Uiso 1 1 d . . . C11 C 0.5827(4) 0.0374(3) 0.2854(2) 0.1295(16) Uani 1 1 d . . . H11A H 0.6323 0.0543 0.2533 0.194 Uiso 1 1 calc R . . H11B H 0.6093 -0.0191 0.3013 0.194 Uiso 1 1 calc R . . H11C H 0.5875 0.0827 0.3155 0.194 Uiso 1 1 calc R . . C12 C 0.3771(5) 0.0005(4) 0.3115(3) 0.193(3) Uani 1 1 d . . . H12A H 0.4089 -0.053 0.3295 0.289 Uiso 1 1 calc R . . H12B H 0.2984 -0.0114 0.2961 0.289 Uiso 1 1 calc R . . H12C H 0.3737 0.0476 0.3403 0.289 Uiso 1 1 calc R . . C13 C 0.4211(3) 0.1973(2) 0.25959(13) 0.0770(8) Uani 1 1 d . . . H13 H 0.465(3) 0.2016(19) 0.2968(13) 0.081(9) Uiso 1 1 d . . . C14 C 0.3771(3) 0.2733(2) 0.23317(14) 0.0767(8) Uani 1 1 d . . . H14 H 0.388(3) 0.329(2) 0.2521(14) 0.095(10) Uiso 1 1 d . . . C15 C 0.3203(3) 0.2685(2) 0.17939(13) 0.0692(7) Uani 1 1 d . . . H15 H 0.293(2) 0.318(2) 0.1605(12) 0.073(8) Uiso 1 1 d . . . C16 C 0.3045(2) 0.18649(17) 0.15064(11) 0.0582(6) Uani 1 1 d . . . C17 C 0.2474(3) 0.1840(2) 0.08932(13) 0.0705(7) Uani 1 1 d . . . H17 H 0.253(3) 0.127(2) 0.0771(15) 0.103(12) Uiso 1 1 d . . . C18 C 0.3212(4) 0.2345(3) 0.04529(16) 0.1218(15) Uani 1 1 d . . . H18A H 0.4012 0.2118 0.0464 0.183 Uiso 1 1 calc R . . H18B H 0.3219 0.2973 0.055 0.183 Uiso 1 1 calc R . . H18C H 0.2873 0.2264 0.0065 0.183 Uiso 1 1 calc R . . C19 C 0.1219(3) 0.2170(4) 0.08846(19) 0.141(2) Uani 1 1 d . . . H19A H 0.0899 0.2141 0.049 0.211 Uiso 1 1 calc R . . H19B H 0.1201 0.2781 0.1021 0.211 Uiso 1 1 calc R . . H19C H 0.075 0.18 0.1137 0.211 Uiso 1 1 calc R . . C20 C 0.6951(2) 0.34936(16) 0.11933(10) 0.0555(6) Uani 1 1 d . . . C21 C 0.7798(2) 0.39498(16) 0.08638(11) 0.0583(6) Uani 1 1 d . . . C22 C 0.7459(3) 0.47426(17) 0.05767(12) 0.0663(7) Uani 1 1 d . . . C23 C 0.6322(3) 0.50719(19) 0.06127(13) 0.0689(7) Uani 1 1 d . . . H23 H 0.610(3) 0.563(2) 0.0409(13) 0.086(9) Uiso 1 1 d . . . C24 C 0.5499(2) 0.46121(18) 0.09368(11) 0.0629(6) Uani 1 1 d . . . C25 C 0.5803(2) 0.38304(19) 0.12243(11) 0.0618(6) Uani 1 1 d . . . H25 H 0.527(2) 0.3499(18) 0.1447(12) 0.069(8) Uiso 1 1 d . . . C26 C 0.7228(2) 0.26416(18) 0.14823(11) 0.0592(6) Uani 1 1 d . . . H26 H 0.658(2) 0.2354(18) 0.1708(12) 0.070(8) Uiso 1 1 d . . . C27 C 0.8444(2) 0.14278(17) 0.17302(11) 0.0583(6) Uani 1 1 d . . . C28 C 0.8119(2) 0.06514(17) 0.14211(11) 0.0598(6) Uani 1 1 d . . . C29 C 0.7614(3) 0.0683(2) 0.07971(12) 0.0704(7) Uani 1 1 d . . . H29 H 0.772(3) 0.132(2) 0.0675(14) 0.097(10) Uiso 1 1 d . . . C30 C 0.8349(4) 0.0119(3) 0.03837(14) 0.1241(15) Uani 1 1 d . . . H30A H 0.801 0.0154 -0.0007 0.186 Uiso 1 1 calc R . . H30B H 0.8351 -0.0495 0.0514 0.186 Uiso 1 1 calc R . . H30C H 0.9151 0.0343 0.0382 0.186 Uiso 1 1 calc R . . C31 C 0.6322(4) 0.0419(4) 0.0775(2) 0.1403(19) Uani 1 1 d . . . H31A H 0.6029 0.0447 0.0376 0.21 Uiso 1 1 calc R . . H31B H 0.5874 0.0825 0.1013 0.21 Uiso 1 1 calc R . . H31C H 0.6238 -0.0182 0.0922 0.21 Uiso 1 1 calc R . . C32 C 0.8297(3) -0.0172(2) 0.17025(13) 0.0696(7) Uani 1 1 d . . . H32 H 0.802(3) -0.071(2) 0.1510(13) 0.087(10) Uiso 1 1 d . . . C33 C 0.8807(3) -0.0219(2) 0.22555(13) 0.0780(8) Uani 1 1 d . . . H33 H 0.891(3) -0.083(2) 0.2413(15) 0.104(11) Uiso 1 1 d . . . C34 C 0.9166(3) 0.0551(2) 0.25372(13) 0.0815(9) Uani 1 1 d . . . H34 H 0.951(3) 0.055(2) 0.2907(14) 0.084(9) Uiso 1 1 d . . . C35 C 0.9000(3) 0.1398(2) 0.22828(12) 0.0712(7) Uani 1 1 d . . . C36 C 0.9384(4) 0.2243(3) 0.26037(16) 0.0961(11) Uani 1 1 d . . . H36 H 0.946(3) 0.272(3) 0.2313(17) 0.113(13) Uiso 1 1 d . . . C37 C 1.0657(4) 0.2186(3) 0.28515(19) 0.1235(15) Uani 1 1 d . . . H37A H 1.119 0.204 0.2541 0.185 Uiso 1 1 calc R . . H37B H 1.0701 0.1727 0.3148 0.185 Uiso 1 1 calc R . . H37C H 1.0879 0.2754 0.3021 0.185 Uiso 1 1 calc R . . C38 C 0.8535(5) 0.2483(4) 0.3077(3) 0.174(3) Uani 1 1 d . . . H38A H 0.8799 0.3024 0.327 0.261 Uiso 1 1 calc R . . H38B H 0.8506 0.2002 0.3359 0.261 Uiso 1 1 calc R . . H38C H 0.7756 0.2576 0.2907 0.261 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1353(8) 0.0762(6) 0.0988(6) -0.0280(4) 0.0100(5) 0.0141(5) Cl2 0.1074(7) 0.1046(7) 0.0972(6) 0.0093(5) -0.0315(5) -0.0482(5) Cl3 0.0905(6) 0.0825(6) 0.1302(7) 0.0349(5) -0.0023(5) -0.0203(4) Cl4 0.0804(5) 0.0942(6) 0.0928(5) -0.0024(4) -0.0089(4) 0.0304(4) O1 0.0750(13) 0.0657(13) 0.0847(14) -0.0139(10) 0.0032(10) -0.0006(10) O2 0.0616(11) 0.0677(13) 0.0902(14) 0.0095(10) -0.0008(10) -0.0014(9) N1 0.0623(12) 0.0525(12) 0.0600(12) -0.0078(9) -0.0047(10) -0.0009(9) N2 0.0642(13) 0.0577(12) 0.0615(12) 0.0041(9) -0.0038(10) 0.0049(10) C1 0.0698(15) 0.0531(14) 0.0456(12) 0.0025(10) -0.0089(11) -0.0065(11) C2 0.0763(17) 0.0489(13) 0.0509(13) 0.0024(10) -0.0075(12) -0.0012(12) C3 0.103(2) 0.0534(15) 0.0550(14) -0.0020(11) -0.0057(14) 0.0018(14) C4 0.114(3) 0.0554(16) 0.0569(15) 0.0001(12) -0.0165(16) -0.0159(16) C5 0.089(2) 0.0698(17) 0.0516(14) 0.0068(12) -0.0184(14) -0.0224(15) C6 0.0748(17) 0.0678(17) 0.0519(13) 0.0026(12) -0.0071(13) -0.0099(14) C7 0.0637(15) 0.0577(15) 0.0524(13) -0.0036(11) -0.0032(12) 0.0001(12) C8 0.0546(13) 0.0558(14) 0.0557(13) -0.0078(10) 0.0020(10) -0.0046(10) C9 0.0729(17) 0.0672(16) 0.0595(14) -0.0055(12) -0.0079(13) -0.0061(13) C10 0.105(3) 0.086(2) 0.076(2) 0.0065(17) -0.0261(19) -0.0033(19) C11 0.103(3) 0.157(4) 0.128(3) 0.027(3) -0.012(3) 0.030(3) C12 0.136(4) 0.207(6) 0.238(7) 0.146(5) 0.044(4) 0.014(4) C13 0.089(2) 0.082(2) 0.0593(16) -0.0145(14) -0.0091(15) -0.0135(16) C14 0.092(2) 0.0660(18) 0.0722(18) -0.0214(15) 0.0040(16) -0.0122(16) C15 0.0770(18) 0.0565(16) 0.0743(18) -0.0051(13) 0.0068(14) -0.0005(13) C16 0.0553(13) 0.0579(15) 0.0613(14) -0.0054(11) 0.0005(11) -0.0009(11) C17 0.0760(18) 0.0681(19) 0.0669(16) 0.0005(14) -0.0110(14) 0.0005(14) C18 0.102(3) 0.189(5) 0.074(2) 0.016(3) -0.002(2) -0.024(3) C19 0.072(2) 0.253(6) 0.097(3) 0.012(3) -0.014(2) 0.024(3) C20 0.0611(14) 0.0551(14) 0.0500(12) -0.0049(10) -0.0068(11) 0.0023(11) C21 0.0601(14) 0.0550(14) 0.0593(14) -0.0071(11) -0.0107(11) -0.0033(11) C22 0.0747(17) 0.0541(15) 0.0697(16) 0.0005(12) -0.0119(13) -0.0097(13) C23 0.0825(19) 0.0496(15) 0.0738(17) -0.0026(12) -0.0170(15) 0.0045(13) C24 0.0673(15) 0.0638(16) 0.0572(14) -0.0093(12) -0.0099(12) 0.0104(12) C25 0.0661(16) 0.0642(16) 0.0548(14) -0.0040(12) -0.0029(12) 0.0040(13) C26 0.0627(15) 0.0622(15) 0.0525(13) 0.0023(11) -0.0015(12) -0.0003(12) C27 0.0576(14) 0.0617(15) 0.0556(13) 0.0085(11) 0.0011(11) 0.0060(11) C28 0.0581(14) 0.0629(15) 0.0583(14) 0.0086(11) 0.0010(11) 0.0036(11) C29 0.0852(19) 0.0641(17) 0.0614(15) 0.0058(13) -0.0125(14) -0.0008(14) C30 0.176(4) 0.136(4) 0.0594(19) -0.001(2) -0.008(2) 0.043(3) C31 0.097(3) 0.203(5) 0.119(3) 0.023(3) -0.043(3) -0.035(3) C32 0.0795(18) 0.0622(17) 0.0672(16) 0.0087(13) 0.0049(14) 0.0039(14) C33 0.095(2) 0.072(2) 0.0678(17) 0.0203(15) 0.0048(15) 0.0167(16) C34 0.096(2) 0.091(2) 0.0571(16) 0.0129(15) -0.0094(16) 0.0151(18) C35 0.0775(18) 0.0770(18) 0.0589(15) 0.0033(13) -0.0062(13) 0.0066(14) C36 0.123(3) 0.089(2) 0.074(2) -0.0055(18) -0.029(2) 0.001(2) C37 0.114(3) 0.153(4) 0.103(3) -0.019(3) -0.013(2) -0.031(3) C38 0.140(4) 0.186(6) 0.197(6) -0.110(5) 0.021(4) 0.008(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C3 1.722(3) . ? Cl2 C5 1.737(3) . ? Cl3 C22 1.729(3) . ? Cl4 C24 1.736(3) . ? O1 C2 1.337(3) . ? O1 H1 0.86(3) . ? O2 C21 1.336(3) . ? O2 H2 0.87(3) . ? N1 C7 1.271(3) . ? N1 C8 1.433(3) . ? N2 C26 1.271(3) . ? N2 C27 1.434(3) . ? C1 C6 1.394(4) . ? C1 C2 1.396(4) . ? C1 C7 1.458(3) . ? C2 C3 1.399(3) . ? C3 C4 1.380(4) . ? C4 C5 1.373(4) . ? C4 H4 0.97(3) . ? C5 C6 1.363(4) . ? C6 H6 0.93(3) . ? C7 H7 0.99(3) . ? C8 C16 1.396(3) . ? C8 C9 1.397(3) . ? C9 C13 1.390(4) . ? C9 C10 1.519(4) . ? C10 C12 1.467(6) . ? C10 C11 1.524(5) . ? C10 H10 1.02(4) . ? C11 H11A 0.96 . ? C11 H11B 0.96 . ? C11 H11C 0.96 . ? C12 H12A 0.96 . ? C12 H12B 0.96 . ? C12 H12C 0.96 . ? C13 C14 1.367(4) . ? C13 H13 0.97(3) . ? C14 C15 1.370(4) . ? C14 H14 0.94(3) . ? C15 C16 1.393(4) . ? C15 H15 0.91(3) . ? C16 C17 1.523(4) . ? C17 C19 1.491(5) . ? C17 C18 1.512(5) . ? C17 H17 0.89(3) . ? C18 H18A 0.96 . ? C18 H18B 0.96 . ? C18 H18C 0.96 . ? C19 H19A 0.96 . ? C19 H19B 0.96 . ? C19 H19C 0.96 . ? C20 C25 1.386(4) . ? C20 C21 1.398(4) . ? C20 C26 1.458(3) . ? C21 C22 1.396(3) . ? C22 C23 1.371(4) . ? C23 C24 1.376(4) . ? C23 H23 0.97(3) . ? C24 C25 1.373(4) . ? C25 H25 0.94(3) . ? C26 H26 1.00(3) . ? C27 C35 1.392(3) . ? C27 C28 1.396(4) . ? C28 C32 1.394(4) . ? C28 C29 1.518(3) . ? C29 C31 1.502(5) . ? C29 C30 1.516(5) . ? C29 H29 0.99(3) . ? C30 H30A 0.96 . ? C30 H30B 0.96 . ? C30 H30C 0.96 . ? C31 H31A 0.96 . ? C31 H31B 0.96 . ? C31 H31C 0.96 . ? C32 C33 1.373(4) . ? C32 H32 0.96(3) . ? C33 C34 1.368(5) . ? C33 H33 0.99(4) . ? C34 C35 1.397(4) . ? C34 H34 0.92(3) . ? C35 C36 1.511(4) . ? C36 C38 1.495(6) . ? C36 C37 1.528(5) . ? C36 H36 0.97(4) . ? C37 H37A 0.96 . ? C37 H37B 0.96 . ? C37 H37C 0.96 . ? C38 H38A 0.96 . ? C38 H38B 0.96 . ? C38 H38C 0.96 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 H1 106(2) . . ? C21 O2 H2 104(2) . . ? C7 N1 C8 119.0(2) . . ? C26 N2 C27 118.4(2) . . ? C6 C1 C2 119.7(2) . . ? C6 C1 C7 119.1(3) . . ? C2 C1 C7 121.1(2) . . ? O1 C2 C1 122.4(2) . . ? O1 C2 C3 119.1(3) . . ? C1 C2 C3 118.5(3) . . ? C4 C3 C2 121.0(3) . . ? C4 C3 Cl1 120.3(2) . . ? C2 C3 Cl1 118.7(2) . . ? C5 C4 C3 119.4(3) . . ? C5 C4 H4 122.6(19) . . ? C3 C4 H4 118.0(19) . . ? C6 C5 C4 121.1(3) . . ? C6 C5 Cl2 119.6(3) . . ? C4 C5 Cl2 119.3(2) . . ? C5 C6 C1 120.3(3) . . ? C5 C6 H6 121.0(16) . . ? C1 C6 H6 118.7(16) . . ? N1 C7 C1 121.5(2) . . ? N1 C7 H7 121.3(15) . . ? C1 C7 H7 117.2(15) . . ? C16 C8 C9 122.4(2) . . ? C16 C8 N1 119.6(2) . . ? C9 C8 N1 117.9(2) . . ? C13 C9 C8 117.3(3) . . ? C13 C9 C10 121.4(3) . . ? C8 C9 C10 121.3(2) . . ? C12 C10 C9 111.7(4) . . ? C12 C10 C11 110.4(4) . . ? C9 C10 C11 112.8(3) . . ? C12 C10 H10 125(2) . . ? C9 C10 H10 106(2) . . ? C11 C10 H10 89(2) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C9 121.3(3) . . ? C14 C13 H13 120.0(17) . . ? C9 C13 H13 118.7(18) . . ? C13 C14 C15 120.4(3) . . ? C13 C14 H14 118.9(19) . . ? C15 C14 H14 121(2) . . ? C14 C15 C16 121.2(3) . . ? C14 C15 H15 121.7(18) . . ? C16 C15 H15 117.1(18) . . ? C15 C16 C8 117.3(2) . . ? C15 C16 C17 119.9(3) . . ? C8 C16 C17 122.8(2) . . ? C19 C17 C18 111.0(3) . . ? C19 C17 C16 112.6(3) . . ? C18 C17 C16 111.5(3) . . ? C19 C17 H17 112(2) . . ? C18 C17 H17 103(2) . . ? C16 C17 H17 106(2) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 119.7(2) . . ? C25 C20 C26 118.8(2) . . ? C21 C20 C26 121.4(2) . . ? O2 C21 C22 119.0(2) . . ? O2 C21 C20 122.4(2) . . ? C22 C21 C20 118.5(2) . . ? C23 C22 C21 121.3(3) . . ? C23 C22 Cl3 120.0(2) . . ? C21 C22 Cl3 118.7(2) . . ? C22 C23 C24 119.4(3) . . ? C22 C23 H23 119.9(18) . . ? C24 C23 H23 120.7(18) . . ? C25 C24 C23 120.8(3) . . ? C25 C24 Cl4 119.5(2) . . ? C23 C24 Cl4 119.7(2) . . ? C24 C25 C20 120.3(3) . . ? C24 C25 H25 123.1(17) . . ? C20 C25 H25 116.6(17) . . ? N2 C26 C20 121.7(2) . . ? N2 C26 H26 121.5(16) . . ? C20 C26 H26 116.8(16) . . ? C35 C27 C28 122.4(2) . . ? C35 C27 N2 118.5(2) . . ? C28 C27 N2 118.9(2) . . ? C32 C28 C27 117.5(2) . . ? C32 C28 C29 120.2(2) . . ? C27 C28 C29 122.3(2) . . ? C31 C29 C30 111.8(3) . . ? C31 C29 C28 111.4(3) . . ? C30 C29 C28 111.4(2) . . ? C31 C29 H29 110.8(18) . . ? C30 C29 H29 106.6(19) . . ? C28 C29 H29 104.4(18) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C33 C32 C28 121.2(3) . . ? C33 C32 H32 119.8(18) . . ? C28 C32 H32 118.9(18) . . ? C34 C33 C32 120.0(3) . . ? C34 C33 H33 125(2) . . ? C32 C33 H33 115(2) . . ? C33 C34 C35 121.7(3) . . ? C33 C34 H34 122.4(19) . . ? C35 C34 H34 115.9(19) . . ? C27 C35 C34 117.1(3) . . ? C27 C35 C36 121.9(3) . . ? C34 C35 C36 121.0(3) . . ? C38 C36 C35 111.5(4) . . ? C38 C36 C37 110.6(4) . . ? C35 C36 C37 112.8(3) . . ? C38 C36 H36 113(2) . . ? C35 C36 H36 108(2) . . ? C37 C36 H36 101(2) . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C36 C38 H38A 109.5 . . ? C36 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C36 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 O1 178.6(2) . . . . ? C7 C1 C2 O1 1.2(4) . . . . ? C6 C1 C2 C3 -0.8(3) . . . . ? C7 C1 C2 C3 -178.1(2) . . . . ? O1 C2 C3 C4 -178.8(2) . . . . ? C1 C2 C3 C4 0.6(4) . . . . ? O1 C2 C3 Cl1 -0.5(3) . . . . ? C1 C2 C3 Cl1 178.85(18) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? Cl1 C3 C4 C5 -178.5(2) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? C3 C4 C5 Cl2 -179.6(2) . . . . ? C4 C5 C6 C1 -0.4(4) . . . . ? Cl2 C5 C6 C1 179.37(19) . . . . ? C2 C1 C6 C5 0.7(4) . . . . ? C7 C1 C6 C5 178.1(2) . . . . ? C8 N1 C7 C1 176.3(2) . . . . ? C6 C1 C7 N1 -177.8(2) . . . . ? C2 C1 C7 N1 -0.4(4) . . . . ? C7 N1 C8 C16 -74.5(3) . . . . ? C7 N1 C8 C9 108.9(3) . . . . ? C16 C8 C9 C13 3.1(4) . . . . ? N1 C8 C9 C13 179.6(2) . . . . ? C16 C8 C9 C10 -179.2(3) . . . . ? N1 C8 C9 C10 -2.7(4) . . . . ? C13 C9 C10 C12 75.7(5) . . . . ? C8 C9 C10 C12 -101.9(4) . . . . ? C13 C9 C10 C11 -49.3(5) . . . . ? C8 C9 C10 C11 133.0(3) . . . . ? C8 C9 C13 C14 -0.8(5) . . . . ? C10 C9 C13 C14 -178.5(3) . . . . ? C9 C13 C14 C15 -1.1(5) . . . . ? C13 C14 C15 C16 0.8(5) . . . . ? C14 C15 C16 C8 1.4(4) . . . . ? C14 C15 C16 C17 -176.5(3) . . . . ? C9 C8 C16 C15 -3.3(4) . . . . ? N1 C8 C16 C15 -179.8(2) . . . . ? C9 C8 C16 C17 174.4(3) . . . . ? N1 C8 C16 C17 -2.1(4) . . . . ? C15 C16 C17 C19 -63.1(4) . . . . ? C8 C16 C17 C19 119.2(4) . . . . ? C15 C16 C17 C18 62.4(4) . . . . ? C8 C16 C17 C18 -115.3(3) . . . . ? C25 C20 C21 O2 -178.4(2) . . . . ? C26 C20 C21 O2 -1.6(4) . . . . ? C25 C20 C21 C22 0.4(3) . . . . ? C26 C20 C21 C22 177.2(2) . . . . ? O2 C21 C22 C23 178.7(2) . . . . ? C20 C21 C22 C23 -0.1(4) . . . . ? O2 C21 C22 Cl3 1.0(3) . . . . ? C20 C21 C22 Cl3 -177.84(18) . . . . ? C21 C22 C23 C24 -0.1(4) . . . . ? Cl3 C22 C23 C24 177.5(2) . . . . ? C22 C23 C24 C25 0.1(4) . . . . ? C22 C23 C24 Cl4 -179.4(2) . . . . ? C23 C24 C25 C20 0.2(4) . . . . ? Cl4 C24 C25 C20 179.68(19) . . . . ? C21 C20 C25 C24 -0.5(4) . . . . ? C26 C20 C25 C24 -177.3(2) . . . . ? C27 N2 C26 C20 -177.2(2) . . . . ? C25 C20 C26 N2 178.2(2) . . . . ? C21 C20 C26 N2 1.5(4) . . . . ? C26 N2 C27 C35 -100.1(3) . . . . ? C26 N2 C27 C28 83.0(3) . . . . ? C35 C27 C28 C32 4.3(4) . . . . ? N2 C27 C28 C32 -179.0(2) . . . . ? C35 C27 C28 C29 -174.5(3) . . . . ? N2 C27 C28 C29 2.3(4) . . . . ? C32 C28 C29 C31 70.5(4) . . . . ? C27 C28 C29 C31 -110.8(4) . . . . ? C32 C28 C29 C30 -55.2(4) . . . . ? C27 C28 C29 C30 123.5(3) . . . . ? C27 C28 C32 C33 -2.0(4) . . . . ? C29 C28 C32 C33 176.7(3) . . . . ? C28 C32 C33 C34 -0.8(5) . . . . ? C32 C33 C34 C35 1.6(5) . . . . ? C28 C27 C35 C34 -3.5(4) . . . . ? N2 C27 C35 C34 179.8(3) . . . . ? C28 C27 C35 C36 177.9(3) . . . . ? N2 C27 C35 C36 1.2(4) . . . . ? C33 C34 C35 C27 0.5(5) . . . . ? C33 C34 C35 C36 179.1(3) . . . . ? C27 C35 C36 C38 102.3(4) . . . . ? C34 C35 C36 C38 -76.2(5) . . . . ? C27 C35 C36 C37 -132.5(3) . . . . ? C34 C35 C36 C37 49.0(5) . . . . ? #===END data_1e _database_code_CSD 200501 _audit_creation_date 2002-12-10T17:05:37-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; N-(3,5-dichlorosalicylidene)-2,4,6-tri-tert-butylaniline ; _chemical_formula_moiety 'C25 H33 Cl2 N1 O1' _chemical_formula_sum 'C25 H33 Cl2 N O' _chemical_formula_weight 434.42 _chemical_compound_source 'synthesis as described' _chemical_melting_point 459 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.8050(4) _cell_length_b 11.6390(3) _cell_length_c 15.6289(4) _cell_angle_alpha 90 _cell_angle_beta 97.0510(10) _cell_angle_gamma 90 _cell_volume 2492.20(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.158 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.275 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.1178 _diffrn_reflns_av_unetI/netI 0.0899 _diffrn_reflns_number 22697 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 5711 _reflns_number_gt 2872 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Rigaku RAXIS-IV' _computing_cell_refinement 'Rigaku RAXIS-IV' _computing_data_reduction 'Rigaku RAXIS-IV' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0826P)^2^+0.7226P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0034(9) _refine_ls_number_reflns 5711 _refine_ls_number_parameters 366 _refine_ls_number_restraints 93 _refine_ls_R_factor_all 0.1867 _refine_ls_R_factor_gt 0.0883 _refine_ls_wR_factor_ref 0.2128 _refine_ls_wR_factor_gt 0.1711 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.298 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.071 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.67306(12) 0.47183(10) -0.02792(8) 0.0872(5) Uani 1 1 d . . . Cl2 Cl 0.77752(10) 0.03381(10) 0.03974(6) 0.0712(4) Uani 1 1 d . . . O1 O 0.6973(2) 0.4126(2) -0.20525(19) 0.0577(8) Uani 1 1 d . . . H1 H 0.707(4) 0.388(4) -0.257(3) 0.098(19) Uiso 1 1 d . . . N1 N 0.7459(2) 0.2816(3) -0.32297(18) 0.0400(7) Uani 1 1 d . . . C1 C 0.7444(3) 0.2165(3) -0.1791(2) 0.0395(9) Uani 1 1 d . . . C2 C 0.7163(3) 0.3248(3) -0.1503(2) 0.0436(9) Uani 1 1 d . . . C3 C 0.7087(3) 0.3394(3) -0.0634(2) 0.0503(11) Uani 1 1 d . . . C4 C 0.7286(3) 0.2516(3) -0.0056(2) 0.0519(11) Uani 1 1 d . . . H4 H 0.725(3) 0.266(3) 0.058(2) 0.053(11) Uiso 1 1 d . . . C5 C 0.7551(3) 0.1451(3) -0.0341(2) 0.0468(10) Uani 1 1 d . . . C6 C 0.7635(3) 0.1279(3) -0.1197(2) 0.0448(10) Uani 1 1 d . . . H6 H 0.782(3) 0.061(3) -0.138(2) 0.050(12) Uiso 1 1 d . . . C7 C 0.7582(3) 0.1987(3) -0.2689(2) 0.0412(9) Uani 1 1 d . . . H7 H 0.785(3) 0.119(3) -0.287(2) 0.043(10) Uiso 1 1 d . . . C8 C 0.7689(3) 0.2668(3) -0.4097(2) 0.0370(9) Uani 1 1 d . . . C9 C 0.6935(3) 0.2431(3) -0.4766(2) 0.0387(9) Uani 1 1 d . . . C10 C 0.5848(3) 0.2310(4) -0.4621(3) 0.0569(11) Uani 1 1 d . . . C11 C 0.5690(6) 0.1229(7) -0.4095(5) 0.092(2) Uani 1 1 d . . . H11A H 0.496(5) 0.111(4) -0.407(3) 0.101(18) Uiso 1 1 d . . . H11B H 0.593(5) 0.051(6) -0.436(5) 0.14(3) Uiso 1 1 d . . . H11C H 0.597(5) 0.124(5) -0.352(4) 0.12(2) Uiso 1 1 d . . . C12 C 0.5492(5) 0.3385(6) -0.4170(5) 0.0826(17) Uani 1 1 d . . . H12A H 0.551(4) 0.408(5) -0.449(4) 0.10(2) Uiso 1 1 d . . . H12B H 0.583(5) 0.341(6) -0.357(5) 0.14(3) Uiso 1 1 d . . . H12C H 0.479(4) 0.329(4) -0.415(3) 0.090(17) Uiso 1 1 d . . . C13 C 0.5187(4) 0.2193(8) -0.5481(4) 0.090(2) Uani 1 1 d . . . H13A H 0.531(4) 0.293(4) -0.586(4) 0.103(19) Uiso 1 1 d . . . H13B H 0.452(4) 0.210(4) -0.536(3) 0.092(17) Uiso 1 1 d . . . H13C H 0.535(4) 0.146(4) -0.584(4) 0.098(19) Uiso 1 1 d . . . C14 C 0.7213(3) 0.2285(3) -0.5588(2) 0.0425(9) Uani 1 1 d . . . H14 H 0.675(3) 0.212(3) -0.602(2) 0.046(11) Uiso 1 1 d . . . C15 C 0.8160(3) 0.2358(3) -0.5769(2) 0.0414(9) Uani 1 1 d D A . C16 C 0.8416(3) 0.2156(4) -0.6690(2) 0.0583(11) Uani 1 1 d DU . . C17A C 0.7995(6) 0.3170(6) -0.7246(3) 0.090(2) Uani 0.836(9) 1 d PDU A 1 H17A H 0.7304 0.3218 -0.7224 0.135 Uiso 0.836(9) 1 calc PR A 1 H17B H 0.8117 0.3055 -0.7831 0.135 Uiso 0.836(9) 1 calc PR A 1 H17C H 0.83 0.387 -0.703 0.135 Uiso 0.836(9) 1 calc PR A 1 C17B C 0.7543(18) 0.201(4) -0.7363(15) 0.105(12) Uani 0.164(9) 1 d PDU A 2 H17D H 0.776 0.1886 -0.7916 0.158 Uiso 0.164(9) 1 calc PR A 2 H17E H 0.7146 0.2687 -0.7383 0.158 Uiso 0.164(9) 1 calc PR A 2 H17F H 0.7168 0.1358 -0.7218 0.158 Uiso 0.164(9) 1 calc PR A 2 C18A C 0.7908(7) 0.1056(6) -0.7055(4) 0.096(3) Uani 0.836(9) 1 d PDU A 1 H18A H 0.7218 0.112 -0.7035 0.144 Uiso 0.836(9) 1 calc PR A 1 H18B H 0.8157 0.0408 -0.6716 0.144 Uiso 0.836(9) 1 calc PR A 1 H18C H 0.8031 0.0951 -0.7641 0.144 Uiso 0.836(9) 1 calc PR A 1 C18B C 0.904(3) 0.105(3) -0.666(2) 0.096(11) Uani 0.164(9) 1 d PDU A 2 H18D H 0.9602 0.1133 -0.6243 0.144 Uiso 0.164(9) 1 calc PR A 2 H18E H 0.9236 0.0909 -0.7219 0.144 Uiso 0.164(9) 1 calc PR A 2 H18F H 0.8653 0.0409 -0.6503 0.144 Uiso 0.164(9) 1 calc PR A 2 C19A C 0.9492(5) 0.2076(10) -0.6724(4) 0.116(4) Uani 0.836(9) 1 d PU A 1 H19A H 0.9613 0.1952 -0.7309 0.174 Uiso 0.836(9) 1 calc PR A 1 H19B H 0.9754 0.1447 -0.6372 0.174 Uiso 0.836(9) 1 calc PR A 1 H19C H 0.9798 0.2779 -0.6513 0.174 Uiso 0.836(9) 1 calc PR A 1 C19B C 0.904(3) 0.317(3) -0.696(2) 0.096(11) Uani 0.164(9) 1 d PDU A 2 H19D H 0.9609 0.3256 -0.6548 0.144 Uiso 0.164(9) 1 calc PR A 2 H19E H 0.8659 0.3866 -0.6977 0.144 Uiso 0.164(9) 1 calc PR A 2 H19F H 0.9229 0.3023 -0.7519 0.144 Uiso 0.164(9) 1 calc PR A 2 C20 C 0.8859(3) 0.2634(3) -0.5097(2) 0.0461(10) Uani 1 1 d . . . H20 H 0.949(3) 0.268(3) -0.5215(19) 0.029(9) Uiso 1 1 d . . . C21 C 0.8663(3) 0.2820(3) -0.4252(2) 0.0385(9) Uani 1 1 d . A . C22 C 0.9529(3) 0.3158(4) -0.3573(2) 0.0528(11) Uani 1 1 d . . . C23 C 1.0342(4) 0.3734(7) -0.3991(3) 0.127(3) Uani 1 1 d . A . H23A H 1.083 0.4017 -0.3551 0.191 Uiso 1 1 calc R . . H23B H 1.0077 0.4363 -0.4343 0.191 Uiso 1 1 calc R . . H23C H 1.0631 0.3187 -0.4342 0.191 Uiso 1 1 calc R . . C24 C 0.9940(5) 0.2090(5) -0.3116(5) 0.128(3) Uani 1 1 d . A . H24A H 1.019 0.1587 -0.3524 0.192 Uiso 1 1 calc R . . H24B H 0.9433 0.1704 -0.2859 0.192 Uiso 1 1 calc R . . H24C H 1.0457 0.2299 -0.2676 0.192 Uiso 1 1 calc R . . C25 C 0.9271(5) 0.4024(7) -0.2902(5) 0.095(2) Uani 1 1 d . A . H25A H 0.987(4) 0.428(4) -0.258(3) 0.082(15) Uiso 1 1 d . . . H25B H 0.883(5) 0.383(5) -0.257(4) 0.13(3) Uiso 1 1 d . . . H25C H 0.913(6) 0.468(6) -0.337(5) 0.16(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1468(14) 0.0509(7) 0.0712(8) -0.0225(6) 0.0421(8) 0.0031(7) Cl2 0.1071(11) 0.0663(7) 0.0409(5) 0.0141(5) 0.0115(6) 0.0025(7) O1 0.088(3) 0.0403(15) 0.0469(16) -0.0014(14) 0.0164(16) 0.0077(14) N1 0.042(2) 0.0455(17) 0.0324(15) -0.0023(14) 0.0056(13) 0.0008(14) C1 0.047(2) 0.0383(19) 0.0355(18) -0.0030(16) 0.0116(16) -0.0037(17) C2 0.049(3) 0.040(2) 0.043(2) -0.0027(18) 0.0104(18) -0.0027(17) C3 0.068(3) 0.041(2) 0.045(2) -0.0130(18) 0.018(2) -0.0097(19) C4 0.068(3) 0.055(3) 0.0340(19) -0.007(2) 0.015(2) -0.014(2) C5 0.060(3) 0.047(2) 0.0334(19) 0.0010(17) 0.0070(19) -0.0083(19) C6 0.058(3) 0.038(2) 0.039(2) -0.0031(18) 0.0097(19) -0.0039(19) C7 0.052(3) 0.040(2) 0.0311(18) -0.0045(16) 0.0042(17) 0.0012(18) C8 0.043(2) 0.0379(19) 0.0304(17) -0.0001(15) 0.0045(16) 0.0053(16) C9 0.041(2) 0.042(2) 0.0328(17) 0.0012(15) 0.0021(16) -0.0028(16) C10 0.043(3) 0.078(3) 0.050(2) -0.002(2) 0.006(2) -0.008(2) C11 0.075(5) 0.108(5) 0.092(5) 0.019(4) 0.004(4) -0.047(4) C12 0.047(4) 0.113(5) 0.088(4) -0.010(4) 0.011(3) 0.018(3) C13 0.042(4) 0.162(7) 0.064(3) -0.008(4) 0.000(3) -0.016(4) C14 0.047(3) 0.044(2) 0.0337(19) -0.0020(17) -0.0067(19) -0.0028(18) C15 0.049(3) 0.045(2) 0.0310(17) -0.0008(16) 0.0057(17) 0.0050(18) C16 0.068(3) 0.076(3) 0.0312(19) -0.0037(19) 0.0063(19) 0.003(2) C17A 0.109(6) 0.118(5) 0.043(3) 0.025(3) 0.011(3) 0.001(4) C17B 0.099(19) 0.17(3) 0.041(15) -0.02(2) 0.000(12) -0.005(16) C18A 0.144(7) 0.096(5) 0.049(4) -0.030(4) 0.024(4) -0.011(5) C18B 0.13(3) 0.107(16) 0.060(17) 0.006(17) 0.065(17) 0.048(17) C19A 0.068(4) 0.239(12) 0.043(3) -0.025(5) 0.019(3) 0.024(5) C19B 0.12(3) 0.109(17) 0.069(19) 0.003(17) 0.053(18) -0.021(16) C20 0.039(3) 0.065(3) 0.0343(19) 0.0037(18) 0.0039(18) 0.004(2) C21 0.038(2) 0.045(2) 0.0319(17) 0.0004(16) 0.0004(16) 0.0034(17) C22 0.038(3) 0.082(3) 0.037(2) -0.008(2) -0.0019(18) -0.004(2) C23 0.073(4) 0.243(9) 0.068(3) -0.030(4) 0.012(3) -0.075(5) C24 0.099(5) 0.116(5) 0.144(6) 0.003(5) -0.085(5) 0.025(4) C25 0.062(4) 0.142(6) 0.079(4) -0.050(5) 0.001(3) -0.027(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C3 1.730(4) . ? Cl2 C5 1.736(4) . ? O1 C2 1.340(4) . ? N1 C7 1.280(4) . ? N1 C8 1.440(4) . ? C1 C6 1.391(5) . ? C1 C2 1.409(5) . ? C1 C7 1.454(5) . ? C2 C3 1.386(5) . ? C3 C4 1.370(6) . ? C4 C5 1.381(5) . ? C5 C6 1.372(5) . ? C8 C21 1.407(5) . ? C8 C9 1.409(5) . ? C9 C14 1.396(5) . ? C9 C10 1.550(6) . ? C10 C11 1.533(7) . ? C10 C13 1.535(7) . ? C10 C12 1.546(7) . ? C14 C15 1.375(5) . ? C15 C20 1.375(5) . ? C15 C16 1.541(5) . ? C16 C19A 1.495(8) . ? C16 C17B 1.509(17) . ? C16 C18A 1.536(7) . ? C16 C17A 1.537(7) . ? C16 C18B 1.546(17) . ? C16 C19B 1.549(17) . ? C20 C21 1.396(5) . ? C21 C22 1.549(5) . ? C22 C24 1.508(7) . ? C22 C23 1.522(6) . ? C22 C25 1.528(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 C8 120.3(3) . . ? C6 C1 C2 119.2(3) . . ? C6 C1 C7 120.1(3) . . ? C2 C1 C7 120.6(3) . . ? O1 C2 C3 120.1(3) . . ? O1 C2 C1 121.2(3) . . ? C3 C2 C1 118.6(4) . . ? C4 C3 C2 121.5(4) . . ? C4 C3 Cl1 119.7(3) . . ? C2 C3 Cl1 118.8(3) . . ? C3 C4 C5 119.8(3) . . ? C6 C5 C4 120.2(4) . . ? C6 C5 Cl2 120.6(3) . . ? C4 C5 Cl2 119.2(3) . . ? C5 C6 C1 120.7(4) . . ? N1 C7 C1 120.5(3) . . ? C21 C8 C9 122.1(3) . . ? C21 C8 N1 118.2(3) . . ? C9 C8 N1 119.6(3) . . ? C14 C9 C8 116.4(4) . . ? C14 C9 C10 120.3(4) . . ? C8 C9 C10 123.3(3) . . ? C11 C10 C13 106.8(5) . . ? C11 C10 C12 110.2(5) . . ? C13 C10 C12 106.4(5) . . ? C11 C10 C9 110.9(4) . . ? C13 C10 C9 111.2(4) . . ? C12 C10 C9 111.1(4) . . ? C15 C14 C9 124.0(4) . . ? C14 C15 C20 116.9(3) . . ? C14 C15 C16 121.1(3) . . ? C20 C15 C16 122.0(4) . . ? C19A C16 C17B 132.8(12) . . ? C19A C16 C18A 110.2(5) . . ? C17B C16 C18A 50.0(19) . . ? C19A C16 C17A 109.6(5) . . ? C17B C16 C17A 58.6(19) . . ? C18A C16 C17A 107.8(5) . . ? C19A C16 C15 112.7(4) . . ? C17B C16 C15 114.4(12) . . ? C18A C16 C15 109.1(4) . . ? C17A C16 C15 107.2(4) . . ? C19A C16 C18B 53.2(18) . . ? C17B C16 C18B 108(3) . . ? C18A C16 C18B 62.6(19) . . ? C17A C16 C18B 145.8(10) . . ? C15 C16 C18B 106.8(10) . . ? C19A C16 C19B 56.8(17) . . ? C17B C16 C19B 108.6(19) . . ? C18A C16 C19B 141.1(11) . . ? C17A C16 C19B 56.2(17) . . ? C15 C16 C19B 109.6(11) . . ? C18B C16 C19B 109(2) . . ? C15 C20 C21 124.1(4) . . ? C20 C21 C8 116.3(3) . . ? C20 C21 C22 117.7(3) . . ? C8 C21 C22 126.0(3) . . ? C24 C22 C23 108.2(5) . . ? C24 C22 C25 109.0(5) . . ? C23 C22 C25 104.5(5) . . ? C24 C22 C21 109.2(4) . . ? C23 C22 C21 111.4(3) . . ? C25 C22 C21 114.3(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 O1 179.9(4) . . . . ? C7 C1 C2 O1 3.0(6) . . . . ? C6 C1 C2 C3 0.1(6) . . . . ? C7 C1 C2 C3 -176.8(4) . . . . ? O1 C2 C3 C4 -179.3(4) . . . . ? C1 C2 C3 C4 0.6(6) . . . . ? O1 C2 C3 Cl1 0.8(6) . . . . ? C1 C2 C3 Cl1 -179.4(3) . . . . ? C2 C3 C4 C5 -1.3(7) . . . . ? Cl1 C3 C4 C5 178.7(3) . . . . ? C3 C4 C5 C6 1.4(7) . . . . ? C3 C4 C5 Cl2 -178.6(3) . . . . ? C4 C5 C6 C1 -0.7(6) . . . . ? Cl2 C5 C6 C1 179.2(3) . . . . ? C2 C1 C6 C5 0.0(6) . . . . ? C7 C1 C6 C5 176.9(4) . . . . ? C8 N1 C7 C1 173.8(4) . . . . ? C6 C1 C7 N1 -176.3(4) . . . . ? C2 C1 C7 N1 0.7(6) . . . . ? C7 N1 C8 C21 -83.7(4) . . . . ? C7 N1 C8 C9 99.2(4) . . . . ? C21 C8 C9 C14 3.7(5) . . . . ? N1 C8 C9 C14 -179.3(3) . . . . ? C21 C8 C9 C10 -177.4(3) . . . . ? N1 C8 C9 C10 -0.4(5) . . . . ? C14 C9 C10 C11 110.9(5) . . . . ? C8 C9 C10 C11 -68.0(6) . . . . ? C14 C9 C10 C13 -7.8(6) . . . . ? C8 C9 C10 C13 173.3(5) . . . . ? C14 C9 C10 C12 -126.2(5) . . . . ? C8 C9 C10 C12 55.0(6) . . . . ? C8 C9 C14 C15 0.1(6) . . . . ? C10 C9 C14 C15 -178.8(4) . . . . ? C9 C14 C15 C20 -2.5(6) . . . . ? C9 C14 C15 C16 178.4(4) . . . . ? C14 C15 C16 C19A -170.2(6) . . . . ? C20 C15 C16 C19A 10.7(7) . . . . ? C14 C15 C16 C17B 6(2) . . . . ? C20 C15 C16 C17B -173(2) . . . . ? C14 C15 C16 C18A -47.5(6) . . . . ? C20 C15 C16 C18A 133.5(5) . . . . ? C14 C15 C16 C17A 69.0(5) . . . . ? C20 C15 C16 C17A -110.0(5) . . . . ? C14 C15 C16 C18B -114(2) . . . . ? C20 C15 C16 C18B 67(2) . . . . ? C14 C15 C16 C19B 128.5(19) . . . . ? C20 C15 C16 C19B -51(2) . . . . ? C14 C15 C20 C21 1.2(6) . . . . ? C16 C15 C20 C21 -179.7(4) . . . . ? C15 C20 C21 C8 2.4(6) . . . . ? C15 C20 C21 C22 -178.4(4) . . . . ? C9 C8 C21 C20 -4.9(5) . . . . ? N1 C8 C21 C20 178.1(3) . . . . ? C9 C8 C21 C22 175.9(3) . . . . ? N1 C8 C21 C22 -1.1(5) . . . . ? C20 C21 C22 C24 -94.2(5) . . . . ? C8 C21 C22 C24 85.0(5) . . . . ? C20 C21 C22 C23 25.3(6) . . . . ? C8 C21 C22 C23 -155.5(5) . . . . ? C20 C21 C22 C25 143.5(5) . . . . ? C8 C21 C22 C25 -37.3(6) . . . . ? #===END